Most reasons I am sure were psychological. Ways to find my way through things I grew up dealing with. Today, the desire is to feel comfortable, because I really do enjoy the way I feel when dressed. A dress or skirt allow the legs to be free with the occasional subtle kiss of fabric as I move about my day. Pantyhose and bra invite a sense of security as they are tight against the body. Heels make me taller, stand up straighter, and just give me a sense of confidence other shoes don't give.